Scaled team from 117 to 919 home starts with AI as thought partner
As Head of Organizational Development at a rapidly scaling homebuilder, he transformed his team's fear of AI into enthusiastic adoption by reframing it as a "thought partner." Through weekly hands-on training, he empowered employees across finance, construction, and admin to build their own AI solutions—from custom GPTs to automated workflows—creating a culture where AI exploration is celebrated and everyone contributes to the company's ambitious growth goals.
TEAM EMPOWERMENT AWARD - PROJECT DESCRIPTION
Multiplying Value Through the "AI as Thought Partner" Revolution
The Challenge
When I started introducing AI to my team, I faced the same wall every organization faces: fear.
"Is this going to replace me?" "I'm not technical enough for this." "This is just a fad."
As Head of Organizational Development at Fifth Avenue Properties—a homebuilder scaling from 117 to 919 home starts this year, with a BHAG of 5,000—I knew we couldn't scale with fear. We needed every person in the organization to embrace AI, not resist it.
So I made a decision: I would teach everyone to see AI as a thought partner, not a threat.
The Approach: AI as Thought Partner
The breakthrough came when I stopped talking about AI as a productivity tool and started talking about it as a thought partner.
Not: "AI will do your job faster." But: "AI will think with you. It will help you see what you're missing. It will make you better at what you already do."
This reframe changed everything. People stopped asking "Will this replace me?" and started asking "How can I use this?"
The Program: Weekly AI Training Sessions
Every week, approximately 12 team members join me for hands-on AI training. We cover practical skills they can use immediately:
Curriculum I've Developed:
1. Writing Effective Prompts — The foundation. How to communicate with AI to get useful responses. Being specific. Providing context. Iterating.
2. Custom GPTs — Building specialized AI assistants for specific tasks. One team member built a Change Order Optimizer that's now used across the construction team.
3. Projects in Claude — Organizing work, maintaining context across conversations, building on previous thinking.
4. Using Agents for Research — How to have AI search, gather, and synthesize information from multiple sources.
5. Web Search & Deep Research — Using AI to find current information, analyze documents, and conduct thorough research.
6. Screenshots for Analysis — Uploading images and documents for AI to analyze, extract data, and identify patterns.
7. Introduction to APIs & MCPs — For those ready to go deeper: how systems connect, and how AI can access live data.
8. Document Writing — Using AI to draft, edit, and improve contracts, proposals, reports, and communications.
9. ongoing AI Topics
The Theme Throughout: Every session reinforces the same message—AI is your thought partner. It's here to think with you, not replace you.
The Multiplier Effect
The training doesn't stop when the session ends. People come to me throughout the week for help with specific challenges. And increasingly, they're exploring on their own—experimenting, discovering, building.
That's the multiplier effect. I'm not just teaching skills. I'm creating a culture where AI exploration is normal, encouraged, and celebrated.
Success Stories
The VP of Finance Our VP of Finance has become one of the most enthusiastic AI adopters in the company. Using material from our training sessions and our ongoing discussions, he now uses ChatGPT extensively in his work,-+ soon will be analyzing financial data, drafting reports, and streamlining accounting workflows. He went from curious to power user.
The Land Development Analyst Our land development person now uses ChatGPT to analyze potential land purchases. Before making recommendations on whether a property is a good acquisition for us, he runs it through AI—evaluating zoning, comparable sales, development potential, and risk factors. AI as a thought partner for million-dollar decisions.
The Kelowna Branch Champion Out in our Kelowna branch, we have a team member who uses ChatGPT extensively. She's become the local AI champion—helping others in that office see what's possible and spreading the thought partner mindset across geographic boundaries.
The Office Admin Turned Automation Builder One of our office admins uses ChatGPT and Claude to help me set up Airtable and manage our administrative systems. But she didn't stop there—she's now coming up with her own automations and using SweetProcess to create standardized SOPs for the company. She went from supporting AI initiatives to driving them.
The Change Order Optimizer A team member built a Custom GPT specifically designed to optimize change orders in construction. It's now used across the team, helping standardize and speed up a process that used to be inconsistent and time-consuming. This wasn't something I built—a team member built it after learning the skills in training.
Strategic Org Design at 30,000 Feet On a flight with our Head of Strategic Organization, we asked: "What's it going to take to scale to 5,000 units?" We pulled up Claude, connected it to Airtable via MCP, and analyzed our current org structure in real-time:
- What redundancies do we have?
- What gaps exist in our org chart?
- What roles do we need to build a successful organization at that scale?
- What would it look like if we leveraged AI to operate leaner?
Claude analyzed our actual data and helped us model scenarios. Strategic planning that used to take weeks of consultant work—done on a flight with AI as our thought partner.
Contracts & Accounting Team members across departments are now using Claude and ChatGPT to help write contracts, draft proposals, and handle accounting tasks. They're not waiting for me to build automations—they're solving their own problems with AI as their thought partner.
Overcoming Skepticism
Not everyone was on board at first. Some people were skeptical—worried about AI, unsure if it was worth learning, concerned about being replaced.
What changed their minds:
1. The thought partner framing — When people understood AI wasn't replacing them but partnering with them, the fear dissolved.
2. Seeing peers succeed — When the VP of Finance started getting results, others paid attention. When a colleague built a Custom GPT, it became real.
3. Immediate practical value — We don't teach theory. We teach skills people can use that afternoon. When someone saves 2 hours on a document, they're hooked.
4. No judgment, just support — People can ask questions without feeling stupid. I meet them where they are.
The skeptics are coming around. They're starting to see the power. And once someone has that first "aha" moment—where AI helps them solve a problem they were stuck on—they become advocates.
The Infrastructure I've Built
Training is just the beginning. I've also built systems that empower the team to work better:
Airtable Forms for Data Entry Sales and construction staff enter information directly through forms. No middleman. No delays. Real-time data flows into our central system where everyone can see it.
Cross-Team Visibility Dashboards give sales visibility into construction progress. Construction can see sales status. Everyone works from the same truth.
Customer Notifications Triggered by Team Actions When a construction team member checks a box marking a milestone complete, customers automatically receive an update. The team's action triggers value—no extra work required.
Automation Problem Collection (Coming Soon) An Airtable form going out to all staff asking: "What repetitive task is eating your time?" Crowdsourcing automation opportunities from the people doing the work. Turning every employee into an automation scout.
The Results
Quantitative:
- ~12 team members in weekly training sessions
- Multiple Custom GPTs built by team members (not me)
- AI adoption across 5+ distinct roles: Finance, Land Development, Admin, Construction, Strategic Planning
- Multiple branches using AI (Calgary HQ + Kelowna)
- Office admin now creating automations and SOPs independently
Qualitative:
- Fear replaced with curiosity
- Skeptics becoming advocates
- "AI as thought partner" embedded in culture
- People exploring and building on their own
- Strategic decisions being made with AI analysis
- Coming to me for help, not permission
- Geographic spread—AI culture extending to remote branches
Tools I Use to Empower the Team
Training & Collaboration:
- Claude (primary teaching tool, MCP connections for live data)
- ChatGPT (Custom GPTs, alternative perspective)
- Hands-on workshops with real business problems
Team Infrastructure:
- Airtable (forms, dashboards, data visibility)
- Notion (documentation, knowledge sharing)
- n8n (automations triggered by team actions)
- SweetProcess (standardized SOPs created by team members)
Resources I Share:
- Custom prompts and templates
- Step-by-step guides
- Access to my Custom GPTs as examples
- Office hours for questions
Key Learnings
1. "Thought partner" changes everything — This framing dissolves fear and opens minds. It's the single most important shift.
2. Teach skills, not theory — Every session should give people something they can use that day. Practical beats theoretical.
3. Celebrate peer success — When a colleague builds something cool, share it. Peer examples are more powerful than instructor examples.
4. Meet people where they are — Some are ready for APIs and MCPs. Some are still learning prompts. Both are valid.
5. Build infrastructure, not just skills — Forms, dashboards, and automations make it easy for people to contribute value without being AI experts.
6. Create permission to explore — People need to know it's okay to experiment, make mistakes, and ask questions.
7. The multiplier matters — Training 12 people who each use AI as a thought partner creates more impact than one expert doing everything.
Relevant URLs
www.fifthavehomes.com, fifthaveproperties.com
Closing
I don't just use AI myself. I teach others to use it. I build systems that make it easy. I create a culture where AI is a thought partner for everyone—not just the technical people, not just leadership, everyone.
The VP of Finance analyzing data with ChatGPT. The land development analyst evaluating million-dollar acquisitions. The office admin building automations and SOPs. The Kelowna branch spreading AI culture 600 kilometers away. Strategic org design happening at 30,000 feet with Claude connected to our live data.
This is what team empowerment looks like.
We're scaling from 117 to 919 homes this year. Our BHAG is 5,000. The only way we get there is if AI isn't just my thought partner—it's everyone's.
I'm building that future, one training session at a time.
note: I didn't have a picture of me teaching in the boardroom so I used Claude to create a prompt for midjourney of an office... just for fun!
Jeff Van Leenen
Written 22 January 2026 Submitted by the storyteller
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